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I met an older woman at a bar last night.

Posted on September 3, 2025 by Joke Poo

She looked pretty good for a 60-year-oid. In fact, she wasn't too bad at all, and I found myself thinking she probably had a really hot daughter.

We drank a couple of beers, and she asked if I'd ever had a Sportsman's Double?
"What's that? I asked. 'It's a mother and daughter threesome, she said.

As my mind began to embrace the idea, and I wondered what her daughter might look like, I said, 'No, I haven't. We drank a bit more, then she said with a wink, 'tonight's your lucky night.

We went back to her place. We walked in. She put on the hall light and shouted upstairs: "Mum…you still awake?'

Joke Poo: The Inheritance

I met an older professor at a conference last week. He looked pretty good for an octogenarian, surprisingly sharp actually. In fact, he was so impressive, I found myself wondering if he had a substantial estate.

We discussed academia and he asked if I’d ever heard of a “Legacy Grant”?

“What’s that?” I asked. “It’s a dual mentorship arrangement – two aspiring academics supported financially by a senior figure,” he said.

As my mind began to entertain the possibilities – reduced teaching load, research funding – I said, “No, I haven’t.” We talked a bit more, then he said with a conspiratorial smile, “Tonight’s your lucky night.”

We went back to his house. He led me to his study, filled with dusty books and antique furniture. He cleared his throat and shouted down the hall: “Agnes… you still alive?”

Alright, let’s dissect this joke!

Key Elements:

  1. Expectation Subversion: The setup leads us to believe the man is pursuing the older woman. The punchline reveals a complete reversal, showing he’s actually the target of a multi-generational pursuit.
  2. Age and Attractiveness: The joke plays on assumptions about age, desirability, and the relative attractiveness of mother and daughter. The “hot daughter” trope is a core element.
  3. Sexual Innuendo and Misinterpretation: The “Sportsman’s Double” line introduces a specific, suggestive term that’s deliberately misinterpreted, creating a humorous misunderstanding.
  4. The “Punchline Reveal”: The “Mum… you still awake?” line is the sudden, unexpected twist that delivers the comedic impact.
  5. The “Sportsman’s Double”: The term is key to the humor as a sexualized term.

Comedic Enrichment & New Material:

Let’s focus on the “Sportsman’s Double” angle. Here’s a new joke leveraging that, along with a “Did You Know” tidbit:

New Joke:

I tried ordering a “Sportsman’s Double” at the bar last night. The bartender just stared blankly. Turns out, it’s not on the official cocktail menu. He did offer me a “Mother’s Milk” instead… which, now that I think about it, might have been even more confusing.

“Did You Know” (Playing on the Cocktail Theme):

Did you know the term “cocktail” itself is shrouded in mystery? While the true origin is debated, one theory links it to the practice of “cock tailing” horses. Horses with docked tails (cocktails) were considered less valuable and thus, were sold for less at market, “cocktailing” their tail being associated with adulteration of the horse. In a similar way, a “cock tail” drink was originally one with bits and pieces, or one that was adulterated with odd mixtures.

Why this works:

  • New Joke: It capitalizes on the specific phrase from the original joke and creates a new, plausible (but slightly absurd) scenario. The “Mother’s Milk” punchline keeps the focus on the family dynamic and awkward sexual innuendo.
  • “Did You Know”: It takes the cocktail element from the punchline and connects it to a surprising and (hopefully) funny historical fact. It subverts expectations (you were probably expecting something about drinking!). By referencing the word “adulteration”, the idea of a “sportsman’s double” becomes even more humorous.

Let me know if you want another one! I’m ready to delve deeper into any aspect of the original joke.

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